13073-29-5

Usage

Synthesis Reference(s)

Synthetic Communications, 16, p. 63, 1986 DOI: 10.1080/00397918608057689

InChI:InChI=1/C7H7NO3/c1-5-3-2-4-6(7(5)9)8(10)11/h2-4,9H,1H3

Upstream product

• 78-30-8 tri-ortho-cresyl phosphate 
• 108-88-3 toluene 
• 95-53-4 o-toluidine 
• 77815-15-7 6-methyl-6-nitrocyclohexa-2,4-dienone 
• 95-48-7 ortho-cresol 
• 17091-93-9 1-methylbenzene oxide 
• 7664-93-9 sulfuric acid 
• 7732-18-5 water 
• 7697-37-2 nitric acid 
• 71-43-2 benzene 
• 7647-01-0 hydrogenchloride 
• 7722-84-1 dihydrogen peroxide 
• 602-01-7 1-methyl-2,3-dinitrobenzene 
• 99-08-1 1-methyl-3-nitrobenzene 

Downstream Products

• 18102-29-9 2-methyl-6-nitroanisole 
• 42585-04-6 C₁₂H₁₈ClN₂O₃PS 
• 158749-49-6 2'-methyl-6'-nitrophenyl acridine-9-carboxylate 
• 488-17-5 3-methylbenzene-1,2-diol 
• 534-52-1 6-methyl-2,4-dinitrophenol 
• 29027-13-2 2-methyl-4,6-dinitroanisole 
• 7477-94-3 2-methyl-4,6-dinitroaniline 
• 56207-35-3 acetic acid-(2-methyl-4,6-dinitro-anilide) 
• 807639-29-8 hexanoic acid, 6-(2-methyl-6-nitrophenoxy)-, methyl ester 
• 889459-02-3 (S)-2-tert-butoxycarbonylamino-3-(2-methyl-6-nitro-phenoxy)-propionic acid benzyl ester 
• 70277-91-7 acetic acid-(2-methyl-6-nitro-phenyl ester) 
• 17672-22-9 2-amino-6-methylphenol 
• 85895-88-1 6-hydroxy-5-nitro-toluene-3-sulfonic acid 

Relevant academic research and scientific papers

Palladium-catalyzed C-O bond formation: direct synthesis of phenols and aryl/alkyl ethers from activated aryl halides

A simple and efficient palladium-catalyzed carbon-oxygen bond formation is reported. The palladium-tri-tert-butylphosphine complex was found to be effective in converting haloarenes to corresponding substituted phenols. This methodology offers a direct transformation of aryl halides to phenols, as well as the straightforward application to generate a wide variety of diaryl or alkyl/aryl ethers.

Calcium nitrate - A new nitrating agent for nuclear nitration of substituted phenols

Nitration of selected substituted phenols using Calcium Nitrate as a new nitrating agent is reported, compared with sodium nitrate and the dependance of product selectivity on temperature is demonstrated.

IPSO NITRATION: NITRATION OF 2-ALKYLPHENOLS IN ACETIC ANHYDRIDE. FORMATION OF 6-ALKYL-6-NITROCYCLOHEXA-2,4-DIENONES

Low temperature nitration of 2-alkylphenols in acetic anhydride gives 6-alkyl-6-nitrocyclohexa-2,4-dienones.The dienones undergo a regiospecific rearrangement to give o-nitrophenols

Studies on photochemical reactions of air pollutants. XIII. Formation of nitrophenols by the reactions of three toluene oxides with nitrogen dioxide in air

Three toluene oxides reacted with nitrogen dioxide in air to give nitrocresols. 1-Methylbenzene oxide (1) and 3-methylbenzene oxide (2) gave the same nitrocresols, including 2-methyl-6-nitrophenol (1b) and 2-methyl-4-nitrophenol (1c), while 4-methylbenzene oxide (3) gave only 4-methyl-2-nitrophenol (3b). Irradiation with a xenon lamp through a Pyrex filter (cut-off below 290 nm) did not affect the product distribution. Only 1-methylbenzene oxide (1) generated fog when it was brought into contact with nitrogen dioxide in air.

Synthesis method of 2-fluoro-3-nitrobenzoic acid intermediate raw material

The invention discloses a synthesis method of a 2-fluoro-3-nitrobenzoic acid intermediate raw material. The invention provides a novel synthesis route, and an important medical intermediate can be rapidly and conveniently prepared from cheap and easily available raw materials. The process method comprises the following steps: starting from o-methylphenol, carrying out nitration reaction to selectively generate a key intermediate 2-methyl-6-nitrophenol, carrying out hydroxyl chlorination to generate 2-chloro-3-nitrotoluene, then carrying out fluorination reaction to generate 2-fluoro-3-nitrotoluene, and finally oxidizing methyl under the action of an oxidant to generate 2-fluoro-3-nitrobenzoic acid. The method is not only high in yield, but also suitable for large-scale production.

Novel SIRT 1 activator and medical use thereof

The present invention relates to an SIRT 1 activator and a medical purpose thereof. According to the present invention, the novel SIRT 1 activator based on a benzo[d]oxazole frame, a hydrate thereof, a crystal form thereof, and salt thereof are manufactured. According to the present invention, it is confirmed that the SIRT 1 activator has improvement effects on obesity, insulin resistance, and dyslipidemia, improvement effect on fatty liver, prevention effects on cell aging and oxidation stress, and collagen composition and wrinkle improvement effect. Therefore, the novel SIRT 1 activator having the same effect can be usefully used as a pharmaceutical composition for preventing or treating a metabolic and liver diseases, a cosmetic composition for preventing or treating wrinkles, and a health food composition for preventing cell aging, wherein the metabolic disease includes obesity, diabetes, and dyslipidemia and the liver disease includes an alcoholic or nonalcoholic fatty liver and fatty hepatitis.COPYRIGHT KIPO 2018

A ortho-nitro phenol and its derivative synthesis method (by machine translation)

The invention relates to a method for the synthesis of organic compounds, in the existing technology of O-nitrophenol strong acid used in the synthesis process of the serious problem of environmental pollution and the synthesis step longer more complicated problem, the invention provides a ortho-nitro phenol and synthetic method of derivative thereof, proceeding by the phenol compound, synthesis of 2 - (phenoxy) pyridine, the obtained product, catalyst, tert-butyl nitrite, organic solvent and adding sealing in the pressure containers, in oil bath heating 50 - 100 °C, reaction 10 - 30 hours, to obtain 2 - (2 - nitrobenzene) ethoxy pyridine; re-processing by the ortho-nitro phenol and its derivatives; the method is simple, high-efficiency. (by machine translation)

An ortho-nitro phenol synthetic method of compound

The invention relates to a synthesis method of o-nitrophenol compounds, solving the problems that production hazards are easily caused due to the release of a large deal of heat during the synthesis of o-nitrophenol and the severe environment pollution caused due to the generation of a large deal of waste gas and acid in the process in the prior art. The invention provides the synthesis method of the o-nitrophenol compounds, which comprises the steps: synthesizing 2-(phenoxy)pyridine from phenol compounds; and then sequentially adding 2-(phenoxy)pyridine and a catalyst, a nitrating reagent, an oxidant and an organic solvent into a sealed pressure container, heating and reacting for 10-50 hours in an oil bath of which the temperature is 80 DEG C-130 DEG C to obtain 2-(2-nitrophenyl)oxy pyridine; and finally treating to obtain o-nitrophenol. The synthesis method is simple, convenient and efficient.

Tertiary Butyl Nitrite Triggered Nitration of Phenols: Solvent- and Structure-Dependent Kinetic Study

Nitration of phenols with tertiary butyl nitrite (TBN) obeyed second-order kinetics with a first-order dependence on [TBN] and [phenol] under acid-free conditions. Reaction rates were significantly altered by a change in the dielectric constant and other physical properties of solvent. The rate of nitration increased with an increase in temperature (303-323 K) in different solvent media (acetonitrile, dichloroethane, CCl4, dimethyl formamide (DMF), and toluene). The rates of nitration (log k) could not fit into either Amis or Kirkwood plots [log k' vs. (1/D) or [(D - 1)/(2D + 1)], but the trends were better explained by the basic form of multivariate linear solvent energy relationships (MLSER) suggested by the Koppel and Palm approach on the one hand and the Kamlet and Taft approach on the other hand. These observations probably substantiate that cumulative contributions of basic solvent parameters (equilibrium as well as frictional solvent effects) and solvent-solute interactions for solvation of transition state during nitration of phenols. Reaction rates accelerated with the introduction of electron-donating groups and retarded with electron-withdrawing groups. Accordingly, the reactivity of structurally different phenols was found to follow the following sequence: p-OH > p-MeO > p-Me > H > m-Me > p-Cl > p-Br > m-Cl > p-NO2 > m-OH. The results are interpreted by Hammett's theory of linear free energy relationship. The reaction constant (Hammett's ρ) is a measure of the sensitivity of the reaction toward the electronic effects of the substituent. The rho (ρ) values obtained from the present experiments are fairly large negative values (ρ CH3) versus σ? or, Es or combined Taft's relationship. However, Charton's MLRA of the log k with polar, resonance, steric, hydrophobicity, and molar refractivity showing a very good linear relationship was obtained. It is of interest to note that when log kexp values are correlated with log kcal a perfect linearity is obtained with a correlation coefficient of unity, indicating the consonance between experimental and calculated rate constants in the present work.

N-methyl-2-chloropyridinium iodide/NaNO2/Wet SiO2: Neutral reagent system for the nitration of activated aromatic compounds under very mild conditions

Mononitration of activated aromatic compounds using N-methyl-2-chloro-pyridinium iodide (Mukaiyama reagent)/NaNO2/wet SiO2 reagent system under neutral, very mild and environmentally safer reaction condition has been developed. Various structurally diverse aromatic rings are subjected in this condition and the corresponding nitro-aromatic compounds are prepared in moderately high yields.